Just tried the trip planning itinerary-maker at plnnr.com. It's free and you can choose from about 20 destinations, mostly European. Florence, Milan, Naples, and Rome are currently available. You pick your date, number of days in the locale, the type of trip (with kids, outdoors, best of, culture) and then choose your intensity level - from light to extreme. Lastly, you choose the number of stars you want for your hotel. The itinerary pops up with a daily route with color photos, trip advisor reviews, and wikipedia info for each of your activities as well as a hotel recommendation near your activities. After customizing the itinerary as much as you want to, you can save and print it.
I chose the moderate intensity level and found it was extreme for me. It'd be cool if you could input the ages of the children you'd be traveling with for more appropriate activities. You can adjust the weight of each item, for instance, make "garden" have the most weight or "museum." All in all, it's easy and fun, especially if you don't like flipping back and forth through guidebooks.
